Ethylamine → HCID 59481301, compound

HRID 560621Notes

Reaction equation

C(N)C1C=CC=CC=1.[CH2:9]([NH2:11])[CH3:10].[CH3:12][C:13]1[N:14]=[C:15]([N:21]2[CH2:25][CH2:24][N:23]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][C:34]([F:37])([F:36])[F:35])=[CH:29][CH:28]=3)[C:22]2=[O:38])[S:16][C:17]=1[C:18](O)=[O:19]>>[CH2:9]([NH:11][C:18]([C:17]1[S:16][C:15]([N:21]2[CH2:25][CH2:24][N:23]([CH2:26][C:27]3[CH:28]=[CH:29][C:30]([O:33][C:34]([F:35])([F:36])[F:37])=[CH:31][CH:32]=3)[C:22]2=[O:38])=[N:14][C:13]=1[CH3:12])=[O:19])[CH3:10]

Participants

Reactant 3

HCID 6341Ethylamine

HCID 7504Benzylamine

HCID 594812844-Methyl-2-(2-oxo-3-(4-(trifluoromethoxy)benzyl)imidazolidin-1-yl)thiazole-5-carboxylic acid

Product 1

HCID 59481301HCID 59481301, compoundYield 25%

Procedure

Following the procedure as describe in Example 8, making variations as required to replace benzylamine with ethylamine to react with 4-methyl-2-(2-oxo-3-(4-(trifluoromethoxy)benzyl)imidazolidin-1-yl)thiazole-5-carboxylic acid, the title compound was obtained as a white powder in 25% yield: mp 218-219° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.32 (d, J=8.4 Hz, 2H), 7.18 (d, J=8.4 Hz, 2H), 5.60 (s, 1H), 4.47 (s, 2H), 4.10-4.04 (m, 2H), 3.51-3.35 (m, 4H), 2.57 (s, 3H), 1.18 (t, J=7.5 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 162.3, 157.0, 155.4, 152.3, 148.9, 134.4, 129.7, 121.4, 120.4, 117.8, 47.3, 42.0, 41.8, 35.1, 34.8, 17.0, 14.8: MS (ES+) m/z 429.2 (M+1).

Sources & evidence

ORD record: ord-98a3721d3b5c4457be344534ae9ff814
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063084B2

Reaction notes

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